JP6437187B2 - 光学活性２級アルコールの製造方法 - Google Patents

光学活性２級アルコールの製造方法 Download PDF

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JP6437187B2
JP6437187B2 JP2013156036A JP2013156036A JP6437187B2 JP 6437187 B2 JP6437187 B2 JP 6437187B2 JP 2013156036 A JP2013156036 A JP 2013156036A JP 2013156036 A JP2013156036 A JP 2013156036A JP 6437187 B2 JP6437187 B2 JP 6437187B2
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Prior art keywords
aminoethyl
aminomethyl
butylpyridine
bis
dimethylpyridine
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JP2013156036A
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Japanese (ja)
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JP2015024976A (ja
Inventor
武昭 片山
武昭 片山
邦彦 堤
邦彦 堤
邦彦 村田
邦彦 村田
毅 大熊
毅 大熊
則義 新井
則義 新井
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Hokkaido University NUC
Kanto Chemical Co Inc
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Hokkaido University NUC
Kanto Chemical Co Inc
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Priority to JP2013156036A priority Critical patent/JP6437187B2/ja
Priority to EP14178338.1A priority patent/EP2865446B1/fr
Priority to US14/340,790 priority patent/US9174906B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24
    • C07C2531/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups C07C2531/02 - C07C2531/24 of the platinum group metals, iron group metals or copper

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
JP2013156036A 2013-07-26 2013-07-26 光学活性２級アルコールの製造方法 Active JP6437187B2 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2013156036A JP6437187B2 (ja) 2013-07-26 2013-07-26 光学活性２級アルコールの製造方法
EP14178338.1A EP2865446B1 (fr) 2013-07-26 2014-07-24 Procédé de production d'alcool secondaire optiquement actif
US14/340,790 US9174906B2 (en) 2013-07-26 2014-07-25 Process for producing optically active secondary alcohol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2013156036A JP6437187B2 (ja) 2013-07-26 2013-07-26 光学活性２級アルコールの製造方法

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JP2018193264A Division JP2019011367A (ja) 2018-10-12 2018-10-12 光学活性２級アルコールの製造方法

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JP6437187B2 true JP6437187B2 (ja) 2018-12-12

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EP (1) EP2865446B1 (fr)
JP (1) JP6437187B2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10190162B2 (en) 2014-10-23 2019-01-29 Complete Genomics, Inc. Signal confinement sequencing (SCS) and nucleotide analogues for signal confinement sequencing
GB201509664D0 (en) 2015-06-03 2015-07-15 Johnson Matthey Plc And Universit Di Udine Process
JP6654960B2 (ja) * 2016-01-15 2020-02-26 日本曹達株式会社 ルテニウム錯体の製造方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2731377B2 (ja) 1994-12-07 1998-03-25 科学技術振興事業団 光学活性アルコール類の製造方法
JP4004123B2 (ja) 1997-12-26 2007-11-07 独立行政法人科学技術振興機構 ルテニウム錯体を触媒とするアルコール化合物の製造方法
JP2001089459A (ja) 1999-09-21 2001-04-03 Sagami Chem Res Center シアノピラジン類の水素添加によるアミノメチルピラジン類の製造方法
JP3566955B2 (ja) * 2001-12-28 2004-09-15 関東化学株式会社 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法
ITPD20040115A1 (it) * 2004-05-04 2004-08-04 Univ Degli Studi Udine Complessi di rutenio con 2-(amminometil)piridine e fosfine, loro preparazione ed uso come catalizzatori
JP5091485B2 (ja) 2004-10-25 2012-12-05 関東化学株式会社 触媒及びこれを用いるｔｅｒｔ−アルキルアルコールの製造方法
US8212037B2 (en) * 2005-03-30 2012-07-03 Kanto Kagaku Kabushiki Kaisha Process for production of optically active quinuclidinols
JP5507931B2 (ja) * 2009-09-01 2014-05-28 関東化学株式会社 芳香族複素環をもつ光学活性アルコールの製造方法

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EP2865446A1 (fr) 2015-04-29
US9174906B2 (en) 2015-11-03
EP2865446B1 (fr) 2021-09-22
JP2015024976A (ja) 2015-02-05
US20150031920A1 (en) 2015-01-29

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